Collective enantioselective total synthesis of (+)-sinensilactam A, (+)-lingzhilactone B and (−)-lingzhiol: divergent reactivity of styrene

• Published in: Chemical communications (Cambridge, England) Vol. 56; no. 69; pp. 166 - 169
• Main Authors: Zhang, Da-Wei, Fan, Hui-Lan, Zhang, Wenzhao, Li, Cheng-Ji, Luo, Sanzhong, Qin, Hong-Bo
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 27.08.2020; Royal Society of Chemistry
• Subjects: Aromatic compounds; Chemistry; Chemistry, Multidisciplinary; Crystallography; Enantiomers; Heterocyclic Compounds, 4 or More Rings - chemical synthesis; Heterocyclic Compounds, 4 or More Rings - chemistry; Physical Sciences; Science & Technology; Stereoisomerism; Styrene - chemistry; Styrenes; Synthesis; Terpenes - chemical synthesis; Terpenes - chemistry; REARRANGEMENT; POTENT; HECK-TYPE REACTION; AZIRIDINES; ACCESS
• ISSN: 1359-7345; 1364-548X
• DOI: 10.1039/d0cc04064a

The collective total synthesis of (+)-sinensilactam A, (+)-lingzhilactone B, (+)-lingzhilactone C and (−)-lingzhiol has been accomplished from a common epoxide intermediate 9 . Chemoselective epoxy opening with either an aryl or alkene moiety of styrene led to different carbon skeletons, which can be advanced to a divergent and concise total synthesis of four meroterpenoids. The collective total synthesis of (+)-sinensilactam A, (+)-lingzhilactone B, (+)-lingzhilactone C and (−)-lingzhiol has been accomplished from a common epoxide intermediate 9.